diff --git a/packages/block-editor/src/components/writing-flow/use-tab-nav.js b/packages/block-editor/src/components/writing-flow/use-tab-nav.js
index 37f69b1c31888..55193839d82d7 100644
--- a/packages/block-editor/src/components/writing-flow/use-tab-nav.js
+++ b/packages/block-editor/src/components/writing-flow/use-tab-nav.js
@@ -94,7 +94,7 @@ export default function useTabNav() {
 				return;
 			}
 
-			if ( event.target.getAttribute( 'aria-pressed' ) === 'true' ) {
+			if ( event.target.shadowRoot ) {
 				return;
 			}
 
diff --git a/packages/e2e-tests/specs/editor/blocks/gallery.test.js b/packages/e2e-tests/specs/editor/blocks/gallery.test.js
index 6c36d687e7a8e..43a277412135f 100644
--- a/packages/e2e-tests/specs/editor/blocks/gallery.test.js
+++ b/packages/e2e-tests/specs/editor/blocks/gallery.test.js
@@ -16,6 +16,15 @@ import {
 	clickButton,
 } from '@wordpress/e2e-test-utils';
 
+async function placeholderUpload() {
+	const input = await page.waitForFunction( () =>
+		document
+			.querySelector( '.wp-block-editor-placeholder' )
+			?.shadowRoot.querySelector( 'input[type="file"]' )
+	);
+	return upload( input );
+}
+
 async function upload( handle ) {
 	const testImagePath = path.join(
 		__dirname,
@@ -42,10 +51,7 @@ describe( 'Gallery', () => {
 
 	it( 'can be created using uploaded images', async () => {
 		await insertBlock( 'Gallery' );
-		const inputHandle = await page.evaluateHandle(
-			`document.querySelector('.wp-block-gallery [role="button"]').shadowRoot.querySelector('input[type="file"]')`
-		);
-		const filename = await upload( inputHandle );
+		const filename = await placeholderUpload();
 
 		const regex = new RegExp(
 			`<!-- wp:gallery {\\"linkTo\\":\\"none\\"} -->\\s*<figure class=\\"wp-block-gallery has-nested-images columns-default is-cropped\\"><!-- wp:image {\\"id\\":\\d+,\\"sizeSlug\\":\\"full\\",\\"linkDestination\\":\\"none\\"} -->\\s*<figure class=\\"wp-block-image size-full\\"><img src=\\"[^"]+\/${ filename }\.png\\" alt=\\"\\" class=\\"wp-image-\\d+\\"\/><\/figure>\\s*<!-- \/wp:image --><\/figure>\\s*<!-- \/wp:gallery -->`
@@ -57,10 +63,7 @@ describe( 'Gallery', () => {
 		const galleryCaption = 'Tested gallery caption';
 
 		await insertBlock( 'Gallery' );
-		const inputHandle = await page.evaluateHandle(
-			`document.querySelector('.wp-block-gallery [role="button"]').shadowRoot.querySelector('input[type="file"]')`
-		);
-		await upload( inputHandle );
+		await placeholderUpload();
 
 		await page.click( '.wp-block-gallery>.blocks-gallery-caption' );
 		await page.keyboard.type( galleryCaption );
@@ -72,10 +75,7 @@ describe( 'Gallery', () => {
 
 	it( "uploaded images' captions can be edited", async () => {
 		await insertBlock( 'Gallery' );
-		const inputHandle = await page.evaluateHandle(
-			`document.querySelector('.wp-block-gallery [role="button"]').shadowRoot.querySelector('input[type="file"]')`
-		);
-		await upload( inputHandle );
+		await placeholderUpload();
 
 		const figureElement = await page.waitForSelector(
 			'.wp-block-gallery .wp-block-image'
diff --git a/packages/e2e-tests/specs/editor/blocks/image.test.js b/packages/e2e-tests/specs/editor/blocks/image.test.js
index 0083476329128..02c121cfad097 100644
--- a/packages/e2e-tests/specs/editor/blocks/image.test.js
+++ b/packages/e2e-tests/specs/editor/blocks/image.test.js
@@ -20,6 +20,15 @@ import {
 	pressKeyWithModifier,
 } from '@wordpress/e2e-test-utils';
 
+async function placeholderUpload() {
+	const input = await page.waitForFunction( () =>
+		document
+			.querySelector( '.wp-block-editor-placeholder' )
+			?.shadowRoot.querySelector( 'input[type="file"]' )
+	);
+	return upload( input );
+}
+
 async function upload( handle ) {
 	const testImagePath = path.join(
 		__dirname,
@@ -63,10 +72,7 @@ describe( 'Image', () => {
 
 	it( 'can be inserted', async () => {
 		await insertBlock( 'Image' );
-		const inputHandle = await page.evaluateHandle(
-			`document.querySelector('.wp-block-image [role="button"]').shadowRoot.querySelector('input[type="file"]')`
-		);
-		const filename = await upload( inputHandle );
+		const filename = await placeholderUpload();
 		await waitForImage( filename );
 
 		const regex = new RegExp(
@@ -77,10 +83,7 @@ describe( 'Image', () => {
 
 	it( 'should replace, reset size, and keep selection', async () => {
 		await insertBlock( 'Image' );
-		const inputHandle = await page.evaluateHandle(
-			`document.querySelector('.wp-block-image [role="button"]').shadowRoot.querySelector('input[type="file"]')`
-		);
-		const filename1 = await upload( inputHandle );
+		const filename1 = await placeholderUpload();
 		await waitForImage( filename1 );
 
 		const regex1 = new RegExp(
@@ -118,10 +121,7 @@ describe( 'Image', () => {
 
 	it.skip( 'should place caret at end of caption after merging empty paragraph', async () => {
 		await insertBlock( 'Image' );
-		const inputHandle = await page.evaluateHandle(
-			`document.querySelector('.wp-block-image [role="button"]').shadowRoot.querySelector('input[type="file"]')`
-		);
-		const fileName = await upload( inputHandle );
+		const fileName = await placeholderUpload();
 		await waitForImage( fileName );
 		await page.keyboard.type( '1' );
 		await page.keyboard.press( 'Enter' );
@@ -135,10 +135,7 @@ describe( 'Image', () => {
 
 	it( 'should allow soft line breaks in caption', async () => {
 		await insertBlock( 'Image' );
-		const inputHandle = await page.evaluateHandle(
-			`document.querySelector('.wp-block-image [role="button"]').shadowRoot.querySelector('input[type="file"]')`
-		);
-		const fileName = await upload( inputHandle );
+		const fileName = await placeholderUpload();
 		await waitForImage( fileName );
 		await page.keyboard.type( '12' );
 		await page.keyboard.press( 'ArrowLeft' );
@@ -151,10 +148,7 @@ describe( 'Image', () => {
 
 	it( 'should have keyboard navigable toolbar for caption', async () => {
 		await insertBlock( 'Image' );
-		const inputHandle = await page.evaluateHandle(
-			`document.querySelector('.wp-block-image [role="button"]').shadowRoot.querySelector('input[type="file"]')`
-		);
-		const fileName = await upload( inputHandle );
+		const fileName = await placeholderUpload();
 		await waitForImage( fileName );
 		// Navigate to More, Link, Italic and finally Bold.
 		await pressKeyWithModifier( 'shift', 'Tab' );
@@ -215,10 +209,7 @@ describe( 'Image', () => {
 	it( 'allows zooming using the crop tools', async () => {
 		// Insert the block, upload a file and crop.
 		await insertBlock( 'Image' );
-		const inputHandle = await page.evaluateHandle(
-			`document.querySelector('.wp-block-image [role="button"]').shadowRoot.querySelector('input[type="file"]')`
-		);
-		const filename = await upload( inputHandle );
+		const filename = await placeholderUpload();
 		await waitForImage( filename );
 
 		// Assert that the image is initially unscaled and unedited.
@@ -263,10 +254,7 @@ describe( 'Image', () => {
 	it( 'allows changing aspect ratio using the crop tools', async () => {
 		// Insert the block, upload a file and crop.
 		await insertBlock( 'Image' );
-		const inputHandle = await page.evaluateHandle(
-			`document.querySelector('.wp-block-image [role="button"]').shadowRoot.querySelector('input[type="file"]')`
-		);
-		const filename = await upload( inputHandle );
+		const filename = await placeholderUpload();
 		await waitForImage( filename );
 
 		// Assert that the image is initially unscaled and unedited.
@@ -303,10 +291,7 @@ describe( 'Image', () => {
 	it( 'allows rotating using the crop tools', async () => {
 		// Insert the block, upload a file and crop.
 		await insertBlock( 'Image' );
-		const inputHandle = await page.evaluateHandle(
-			`document.querySelector('.wp-block-image [role="button"]').shadowRoot.querySelector('input[type="file"]')`
-		);
-		const filename = await upload( inputHandle );
+		const filename = await placeholderUpload();
 		await waitForImage( filename );
 
 		// Assert that the image is initially unscaled and unedited.
@@ -337,10 +322,7 @@ describe( 'Image', () => {
 		await insertBlock( 'Image' );
 
 		// Upload an initial image.
-		const inputHandle = await page.evaluateHandle(
-			`document.querySelector('.wp-block-image [role="button"]').shadowRoot.querySelector('input[type="file"]')`
-		);
-		const filename = await upload( inputHandle );
+		const filename = await placeholderUpload();
 
 		// Resize the Uploaded Image.
 		await openDocumentSettingsSidebar();
@@ -385,10 +367,7 @@ describe( 'Image', () => {
 
 	it( 'should undo without broken temporary state', async () => {
 		await insertBlock( 'Image' );
-		const inputHandle = await page.evaluateHandle(
-			`document.querySelector('.wp-block-image [role="button"]').shadowRoot.querySelector('input[type="file"]')`
-		);
-		const fileName = await upload( inputHandle );
+		const fileName = await placeholderUpload();
 		await waitForImage( fileName );
 		await pressKeyWithModifier( 'primary', 'z' );
 		// Expect an empty image block (placeholder) rather than one with a
diff --git a/packages/e2e-tests/specs/widgets/customizing-widgets.test.js b/packages/e2e-tests/specs/widgets/customizing-widgets.test.js
index c5005d10cf562..6b620ffbd13b5 100644
--- a/packages/e2e-tests/specs/widgets/customizing-widgets.test.js
+++ b/packages/e2e-tests/specs/widgets/customizing-widgets.test.js
@@ -539,12 +539,10 @@ describe( 'Widgets Customizer', () => {
 		await footer1Section.click();
 
 		const legacyWidgetBlock = await addBlock( 'Legacy Widget' );
-		const selectLegacyWidgets = await page.evaluateHandle( () =>
+		const selectLegacyWidgets = await page.waitForFunction( () =>
 			document
-				.querySelector(
-					'.wp-block-legacy-widget [aria-label="Legacy Widget"]'
-				)
-				.shadowRoot.querySelector( 'select' )
+				.querySelector( '.wp-block-editor-placeholder' )
+				?.shadowRoot.querySelector( 'select' )
 		);
 		await selectLegacyWidgets.select( 'test_widget' );